JP2009521557A - Short-chain polyether for rigid polyurethane foam - Google Patents

Abstract

The present invention provides for the presence of a base catalyst having at least one cation chelated with from about 0.5% to about 20% by weight of polyoxyethylene-containing compound, the weight percent being based on the weight of the short chain polyether polyol. Below, there is provided a short chain polyether polyol having a number average molecular weight of less than about 1,200 g / mole prepared by alkoxylation of an initiator. The short chain polyols of the present invention can be used to produce rigid polyurethane foams and non-foamed polyurethanes.

Description

  The present invention generally comprises an initiator in the presence of a polyether polyol, and more particularly a base catalyst having at least one cation chelated with from about 0.5% to about 20% by weight of a polyoxyethylene-containing compound. It relates to short-chain polyether polyols produced by alkoxylation and having a molecular weight of less than about 1,200 g / mol.

  For a long time it has been known that cyclic ethers strongly complex potassium ions. Crown ether was discovered by Charles Pederson in the 1960s, and in 1987 he received the Nobel Prize for his efforts. The ability of cyclic ethers to strongly complex metal ions has led to many scientific studies. Unfortunately, crown ethers have been difficult to manufacture, are expensive, and are toxic and have not found widespread commercial use. Perhaps because crown ethers were first discovered, many skilled artisans have overlooked the strong complexing ability of acyclic polyethers. Among its advantages are the availability, low cost, and the fact that ethylene oxide polymers and oligomers are non-toxic and therefore acceptable for use as food additives.

  The concept of using polyethylene glycol (`` PEG '') to increase the rate of KOH-catalyzed alkoxylation of long chain polyols is known in the art (see `` Synthesis by Mihail Ionescu, Viorica Zugravu, Ioana Mihalache and Ion Vasile). of Polyether Polyols for Flexible Polyurethane Forms with Complexed Counter-Ion ”, Cellular Polymers IV, International Conference, 4th, Shrewsbury, UK, June 5-6, 1997, Paper 8, 1-8. , JM), there is no report that extends this concept to the synthesis of short-chain polyols.

  US patent application filed on the same date as the present application by the same name: “Base-catalyzed alkoxylation in the presence of a polyoxyethylene-containing compound” (Attorney Docket No. PO8708, US patent application number unknown) Disclosed is the molecular weight dependence of polyoxyethylene-containing additives that act as chelating agents in catalytic alkoxylation.

  US patent application filed on the same date by the same applicant as the second application: the title “base catalyzed alkoxylation in the presence of a non-linear polyoxyethylene-containing compound” (lawyer docket number PO8709, US patent application number unknown) is: Disclosed is a non-linear, at least trifunctional polyoxyethylene-containing additive that does not adversely affect the flexible foam produced therefrom as a chelating agent for base-catalyzed alkoxylation of long-chain polyethers .

  Finally, a US patent application filed on the same date as the third application, named “Long-Chain Polyether Polyol” (Attorney Docket No. PO8706, US Patent Application No. Unknown) is chelated in alkoxylation of long-chain polyethers. A polyoxyethylene-containing initiator is disclosed as an agent.

  Short chain polyol starter mixtures are typically mixtures of polyhydroxyl or polyamino functional starters (e.g., propylene glycol, glycerin, trimethylol propane, ethylene diamine, toluene diamine, sucrose, sorbitol) having a functionality in the range of 2-8. Contained and often contains water. It has not been known how such PEGs affect the base-catalyzed synthesis of short-chain polyols (i.e. those having a molecular weight of less than about 1200 g / mol) from these mixtures. It was.

Accordingly, the present invention provides a base catalyst having at least one cation chelated with from about 0.5% to about 20% by weight of a polyoxyethylene-containing compound, the weight percent being based on the weight of the short chain polyether polyol. By providing short chain polyether polyols having a number average molecular weight of less than about 1,200 g / mol, prepared by alkoxylating the initiator in the presence of
The short chain polyols of the present invention can be used to provide rigid polyurethane foams and non-foamed polyurethanes.

  These and other advantages and benefits of the present invention will become apparent from the following detailed description of the invention.

  It is described for purposes of illustration and not limitation. Unless otherwise stated or indicated otherwise, all numbers such as amounts, percentages, OH numbers, functionalities, etc. given herein are in each case modified by the term “about”. Should be understood. The equivalent weights and molecular weights indicated herein are number average equivalent weight and number average molecular weight, respectively, unless otherwise indicated.

  In the presence of a base catalyst having at least one cation chelated with a polyoxyethylene-containing compound of 0.5 wt% to 20 wt% (where wt% is based on the weight of the short-chain polyether polyol). Provided is a short chain polyether polyol having a number average molecular weight of less than 1,200 g / mole produced by alkoxylation of an initiator.

  The present invention is a method for producing a short-chain polyether polyol having a number average molecular weight of less than 1,200 g / mol, comprising 0.5 wt% to 20 wt% (the wt% is based on the weight of the short-chain polyether polyol) Further provided is a method comprising alkoxylating an initiator in the presence of a base catalyst having at least one cation chelated with a polyoxyethylene-containing compound.

Furthermore, the present invention comprises at least one polyisocyanate and
The initiator is alkoxylated in the presence of a base catalyst having at least one cation chelated with a polyoxyethylene-containing compound of 0.5 wt% to 20 wt% (where wt% is based on the weight of the short chain polyether polyol). With at least one short-chain polyether polyol having a number average molecular weight of less than 1,200 g / mol produced by
Optionally in the presence of at least one of blowing agents, surfactants, other cross-linking agents, extenders, pigments, flame retardants, catalysts and fillers,
A rigid polyurethane foam made from the reaction product is provided.

The present invention also includes at least one polyisocyanate,
The initiator is alkoxylated in the presence of a base catalyst having at least one cation chelated with a polyoxyethylene-containing compound of 0.5 wt% to 20 wt% (where wt% is based on the weight of the short chain polyether polyol). At least one short-chain polyether polyol having a number average molecular weight of less than 1,200 g / mol produced by
Optionally in the presence of at least one of blowing agents, surfactants, other cross-linking agents, extenders, pigments, flame retardants, catalysts and fillers,
There is further provided a method of producing a rigid polyurethane foam comprising reacting.

  Here, the “short chain” polyether polyol by the present inventor is a polyether polyol having a number average molecular weight of less than 1,200 g / mol, preferably 300 to 1,000 g / mol, more preferably 500 to 900 g / mol. means. The molecular weight of the polyols of the present invention can be an amount that is in the range (including the quoted values) between any combination of these values.

  The short-chain polyether polyol of the present invention is produced by a base catalyzed reaction. The general conditions for this reaction are well known to those skilled in the art. The base catalyst may be any base catalyst known in the art. More preferably, the base catalyst is one of potassium hydroxide, sodium hydroxide, barium hydroxide and cesium hydroxide, and most preferably the base catalyst is potassium hydroxide.

Suitable initiator compounds include, but are not limited to, C ₁ -C ₃₀ monool, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, neopentyl glycol, 1,3-propanediol. 1,4-butanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 1,6-hexanediol, water, glycerin, trimethylolpropane, trimethylolethane, ethylenediamine, Toluenediamine isomer mixture, pentaerythritol, α-methyl glucoside, sorbitol, mannitol, hydroxymethyl glucoside, hydroxypropyl glucoside, sucrose, N, N, N ′, N′-tetrakis [2-hydroxyethyl or 2-hydroxypropyl] Ethylenediamine 1,4-cyclohexanediol, cyclohexanedimethanol, hydroquinone, resorcinol and the like. The nominal initiator functionality (which is understood to represent the ratio between the total number of equivalents of active hydrogen (determined by the Zerevitnov method) and moles in the starter mixture) is 1-8 or more, preferably 3-6. The functionality of the initiator useful in the present invention can be in an amount that is within the range (including the quoted values) between any combination of these values. Also, any mixture of monomer initiators or their oxyalkylated oligomers may be used. A preferred initiator compound for the short chain polyether polyols of the present invention is a mixture of propylene glycol, sucrose and water having a functionality of 4-6.

  During alkoxylation in the process for producing short chain polyether polyols of the present invention, a polyoxyethylene-containing compound (eg, polyethylene glycol) is added to chelate at least one of the base catalyst cations. Polyoxyethylene-containing compounds suitable for the present invention are understood to be ethoxylates of alcohols, diols or polyols such as polyethylene glycol (PEG) or TPEG (available from Dow Chemical). The polyoxyethylene-containing compound preferably has a hydroxy functionality of 1-8, more preferably 2-6 and most preferably 2-3. Alternatively, the hydroxy functionality of the polyoxyethylene-containing compound may be capped with an alkyl (preferably methyl) group, as is known to those skilled in the art. The functionality of the polyoxyethylene-containing compound can be in an amount that is in the range (including the quoted values) between any combination of these values. The polyoxyethylene-containing compound preferably has a molecular weight of 150 to 1,200, more preferably 200 to 1,000 and most preferably 250 to 400. The polyoxyethylene-containing compound may have an amount of molecular weight that is in the range (including the quoted values) between any combination of these values.

  The polyoxyethylene-containing compound is preferably added in an amount of 0.5 to 20% by weight, more preferably in an amount of 1 to 10% by weight, and most preferably in an amount of 2 to 7% by weight. Based on the final weight of the chain polyether polyol). The polyoxyethylene-containing compound can be added in an amount that is in the range (including the quoted values) between any combination of these values.

Alkylene oxides useful for alkoxylating the initiator to produce the short chain polyether polyols of the present invention include, but are not limited to, ethylene oxide, propylene oxide, oxetane, 1,2- and 2,3-butylene oxide, isobutylene. Oxides, epichlorohydrins, cyclohexene oxides, styrene oxides, and higher alkylene oxides (eg, C ₅ -C ₃₀ α-alkylene oxides). Preference is given to propylene oxide alone or a mixture of propylene oxide and ethylene oxide or another alkylene oxide. Similarly for other polymerizable monomers, such as anhydrides and other monomers as disclosed in U.S. Patents 3,404,109, 3,538,043 and 5,145,883, the contents of which are hereby incorporated by reference in their entirety. Can be used.

  The short-chain polyether polyols of the present invention preferably react with polyisocyanates in the presence of blowing agents, surfactants, cross-linking agents, extenders, pigments, flame retardants, catalysts and fillers as required. Polyurethane foam can be produced.

Suitable polyisocyanates are known to those skilled in the art and include non-modified isocyanates, modified polyisocyanates, and isocyanate prepolymers. Such organic polyisocyanates include, for example, aliphatic, cycloaliphatic, araliphatic, aromatic, of the type described by W. Siefken in Justus Liebigs Annalen der Chemie, 562, pp. 75-136. And heterocyclic polyisocyanates. Examples of such isocyanates include the formula:
Q (NCO) _n
[Wherein n is a number of 2 to 5, preferably 2 to 3, and Q is an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an araliphatic hydrocarbon group or an aromatic hydrocarbon group. . ]
The thing represented by is mentioned.

Examples of suitable isocyanates include the following:
1,4-tetramethylene diisocyanate; 1,6-hexamethylene diisocyanate; 1,12-dodecane diisocyanate; cyclobutane-1,3-diisocyanate; cyclohexane-1,3- and -1,4-diisocyanate, and these 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate; German Patent Publication 1,202,785 and US Patent 3,401,190); 2,4- and 2,6-hexahydro Toluene diisocyanate and mixtures of these isomers; dicyclohexylmethane-4,4′-diisocyanate (hydrogenated MDI or HMDI); 1,3- and 1,4-phenylene diisocyanate; 2,4- and 2,6-toluene diisocyanate and Mixtures of these isomers (TDI); diphenylmethane-2,4'- and / or -4,4'-diisocyanate (MDI) Polymer diphenylmethane diisocyanate (PMDI), naphthylene-1,5-diisocyanate; triphenylmethane-4,4 ', 4''-triisocyanate; types obtainable by condensation of aniline with formaldehyde followed by phosgenation Polyphenyl-polymethylene-polyisocyanates (crude MDI, these are described, for example, in British patents GB 878,430 and GB 848,671); norbornane diisocyanates, such as those described in US Pat. No. 3,492,330; M- and p-isocyanatophenylsulfonyl isocyanates of the type described; for example perchlorinated aryl polyisocyanates of the type described in US Pat. No. 3,227,138; modified polyisocyanates containing carbodiimide groups of the type described in US Pat. No. 3,152,162; For example, U.S. Pat. Modified polyisocyanates containing urethane groups of the type described in 164 and 3,644,457; for example modified polyisocyanates containing allophanate groups of the type described in British patent GB 994,890, Belgian patent BE 761,616 and Dutch patent NL 7,102,524; Isocyanurate group-containing modified polyisocyanates of the type described in U.S. Patent 3,002,973, German Patents 1,022,789, 1,222,067 and 1,027,394 and German Patent Application Publications 1,919,034 and 2,004,048; Polyisocyanates; for example, biuret group-containing polyisocyanates of the type described in German Patents 1,101,394, US Pat. Nos. 3,124,605 and 3,201,372, and British Patent GB 889,050; for example by short chain polymerization reactions of the type described in US Pat. Polyisocyanates obtained; examples Ester group-containing polyisocyanates of the type described in British patents GB 965,474 and GB 1,072,956, US Pat. No. 3,567,763, and German Patent 1,231,688; reaction products of the above isocyanates and acetals as described in German Patent 1,072,385 And polymeric fatty acid group-containing polyisocyanates of the type described in US Pat. No. 3,455,883. It is also possible to use an isocyanate-containing distillation residue which is accumulated in the production of isocyanates on a commercial scale, and optionally in the form of a solution in one or more of the above polyisocyanates. Polymer diphenylmethane diisocyanate is particularly preferred. Those skilled in the art will also recognize that mixtures of the above polyisocyanates can be used.

  Prepolymers can also be used to make the foams of the present invention. The prepolymer contains an excess of organic polyisocyanate or a mixture thereof and a small amount of active hydrogen as determined by the well-known Celebitinov test described by Kohler in the Journal of the American Chemical Society, 49, 3181 (1927). It can be produced by reacting with a compound. These compounds and methods for their production are known to those skilled in the art. The use of any one particular active hydrogen compound is not critical. Any such compound can be used in the practice of the present invention.

  Suitable additives contained as necessary in the rigid polyurethane foam-forming formulation of the present invention include, for example, stabilizers, catalysts, cell regulators, reaction inhibitors, plasticizers, fillers, cross-linking agents or increasing amounts. Agents, foaming agents and the like.

  Stabilizers that may be suitable for the foam forming method of the present invention are, for example, polyether siloxanes, preferably those that are insoluble in water. Such compounds usually have a structure in which a relatively short-chain copolymer of ethylene oxide and propylene oxide is bonded to a polydimethylsiloxane residue. Such stabilizers are described, for example, in US Patents 2,834,748, 2,917,480, and 3,629,308.

  Suitable catalysts for the foam forming method of the present invention include those known in the art. These catalysts include, for example, tertiary amines such as triethylamine, tributylamine, N-methylmorpholine, N-ethylmorpholine, N, N, N ', N'-tetramethylethylenediamine, pentamethyl-diethylenetriamine and higher Homologues (e.g. those described in DE-A 2,624,527 and 2,624,528), 1,4-diazabicyclo (2.2.2) octane, N-methyl-N'-dimethyl-aminoethylpiperazine, bis- (Dimethylaminoalkyl) piperazine, N, N-dimethylbenzylamine, N, N-dimethylcyclohexylamine, N, N-diethyl-benzylamine, bis- (N, N-diethylaminoethyl) adipate, N, N, N ′ , N'-Tetramethyl-1,3-butanediamine, N, N-dimethyl-β-phenylethylamine, 1,2-dimethylimidazole, 2-methylimidazole, monocyclic and bicyclic Min and bis - (dialkylamino) alkyl ethers, such as 2,2-bis - (dimethylaminoethyl) ether.

  Other suitable catalysts that can be used to produce the polyurethane foams of the present invention include, for example, organometallic compounds, especially organotin compounds. Organotin compounds that are considered suitable include sulfur-containing organotin compounds. Examples of such a catalyst include di-n-octyltin mercaptide. Other types of suitable organotin catalysts include preferably tin (II) salts of carboxylic acids such as tin (II) acetate, tin (II) octoate, tin (II) ethylhexoate and / or tin ( II) laurate and the like, and tin (IV) compounds such as dibutyltin oxide, dibutyltin dichloride, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin maleate and / or dioctyltin diacetate.

Although water alone or water can be used in combination with a foaming aid ("ABA"), preferably ABA is used in the foam produced according to the present invention. ABA is well known in the field for producing rigid foams, and ABA includes hydrocarbons, fluorocarbons, hydrofluorocarbons, hydrochlorocarbons, hydrochlorofluorocarbons, chlorofluorocarbons, and carbon dioxide. It is done. Suitable blowing agents include, but are not limited to, HCFC-141b (1-chloro-1,1-difluoroethane), HCFC-22 (monochlorodifluoromethane), HFC-245fa (1,1,1,3,3-penta Fluoropropane), HFC-134a (1,1,1,2-tetrafluoroethane), HFC-365mfc (1,1,1,3,3-pentafluorobutane), cyclopentane, normal pentane, isopentane, LBL- 2 (2-chloropropane), _{trichlorofluoromethane, CCl 2 FCClF 2, CCl 2} FCHF 2, trifluoromethyl chloropropane, 1-fluoro-1,1-dichloroethane, 1,1,1-trifluoro-2,2-dichloroethane, Mention may be made of methylene chloride, diethyl ether, isopropyl ether, methyl formate, carbon dioxide and mixtures thereof.

  When contained, water acts as a blowing agent by chemically forming carbon dioxide gas and amine moieties (which further react with polyisocyanates to form urea backbone groups) by reacting with the isocyanate component. To do.

  The invention is further illustrated, but not limited, by the following examples. All amounts given in “parts” and “%” are understood to be by weight unless otherwise indicated.

  PEG-300, PEG-400, and PEG-600 are polyethylene glycols having number average molecular weights of 300, 400, and 600 g / mol, respectively, and are commercially available from Aldrich Chemical Company. TPEG-990 is an ethoxylated glycerin having a number average molecular weight of 990 g / mol, commercially available from Dow Chemical Company.

(Examples 1 to 8)
A sucrose / propylene glycol / water-initiated polyether was prepared according to the following procedure using the amount of each component (value in grams) specified in Table I. Control experiments were performed without using any polyoxyethylene-containing compounds (Examples C-1 and C-2). Examples 3-8 were prepared according to the present invention. Examples 3-8 contained the indicated polyoxyethylene-containing compounds.

  In all cases, water, KOH solution, propylene glycol, sucrose, and PEG additives (eg, prepared according to the present invention) were charged into a 5 gallon polyether polyol reactor. The reactor was pressurized to 40 psia with nitrogen, evacuated to 20 psia, and this was repeated three times to remove oxygen. The vacuum valve to the reactor was closed and the mixture was heated to 100 ° C. Nitrogen was added to the reactor until a pressure of 20 psia was reached. Feeding of propylene oxide (PO) into the reactor was started. The PO feed rate was controlled by a feedback loop to maintain a total reactor pressure of 45 psia. The grams of PO shown in Table I as PO-1 were added, the feed was stopped, and heated until the pressure drop indicating that the PO was consumed stopped. The time required for PO addition was recorded. The vacuum valve to the reactor was opened and the reaction mixture was dehydrated by heating under full vacuum.

  Dehydration was continued at 100 ° C. until the amount of water reached 1.95-2.0% (determined by Karl Fischer titration). If necessary, water was added to the reaction mixture to bring the water content within this range. The mixture was heated to 110 ° C., enough nitrogen was added to bring the reactor pressure to 20 psia, and the second PO feed (PO-2) was started. The temperature was increased linearly to 120 ° C. over the first 120 minutes of feeding. Again, the PO feed rate was controlled by a feedback loop to maintain a total reactor pressure of 45 psia during the feed. The total PO addition time determined by recording the time required for the second PO addition and summing the time required for both PO feeds is shown in Table II. Sulfuric acid was added to neutralize the KOH, the product was filtered and characterized by viscosity at 25 ° C., hydroxyl number and appearance (turbid or non-turbid).

  As can be better understood with reference to Tables I and II below, in Examples 3 and 4, TPEG-990 (3%) is added to the reaction mixture and sucrose (Example 3) or propylene glycol (Examples). The same number of equivalents of any of 4) was excluded. At the same KOH catalyst level as Comparative Example C-1 (0.3%), the propoxylation time was reduced from 15 hours to about 10 hours. In Examples 5-8, various polyoxyethylene-containing additives were added according to the present invention and the same number of equivalents of propylene glycol was removed. The propoxylation time was reduced between 6 hours and 7.3 hours from 9 hours of the control (Example C-2; KOH = 0.7%) at the same KOH level. This corresponds to a reduction in feed time of approximately 20-30% at 0.7% KOH level and 0.3% KOH level, respectively.

  Over the molecular weight range of 300-1,000 g / mol, it appeared that there was little molecular weight dependence of the rate-accelerating effectiveness of polyoxyethylene-containing additives. However, the low molecular weight oxyethylene-containing additive (PEG-300) produced a sample that was not turbid, while the high molecular weight additive most often produced a turbid sample.

(Examples 9 to 15)
A sucrose / water-initiated polyether was prepared according to the following procedure using the amount of each component (value in grams) specified in Table III. Control experiments were performed without using any polyoxyethylene-containing additive (Examples C-9, C-10 and C-11). Examples 12-15 were prepared according to the present invention. Examples 12-15 contained the indicated polyoxyethylene-containing additives.

  In all cases, water, KOH solution, sucrose, and polyoxyethylene-containing additives (eg, prepared according to the present invention) were charged into a 5 gallon polyether polyol reactor. The reactor was purged with nitrogen by pressurizing to 40 psia with nitrogen, evacuating to 20 psia, and repeating this three times. The vacuum valve to the reactor was closed and the mixture was heated to 100 ° C. Nitrogen was added to the reactor until a pressure of 20 psia was reached. Feeding of propylene oxide (PO) into the reactor was started. The PO feed rate was controlled by a feedback loop to maintain a total reactor pressure of 45 psia. The grams of PO shown in Table III (gram values) as PO-1 were added, the feed was stopped, and heated until the pressure drop indicating that the PO was consumed stopped. The time required for PO addition was recorded. The vacuum valve to the reactor was opened and the reaction mixture was dehydrated by heating under full vacuum.

  Dehydration was continued at 100 ° C. until the water volume reached 0.40-0.45% (determined by Karl Fischer titration). If necessary, water was added to the reaction mixture to bring the water content within this range. Sufficient nitrogen was added to bring the reactor pressure to 20 psia and the second PO feed (PO-2) was started. The temperature was increased linearly to 120 ° C. over the first 120 minutes of feeding. Again, the PO feed rate was controlled by a feedback loop to maintain a total reactor pressure of 45 psia during the feed. The total PO addition time determined by recording the time required for the second PO addition and summing the time required for both PO feeds is shown in Table IV. Sulfuric acid or lactic acid (see Table IV) was added to neutralize the KOH. For sulfuric acid neutralized samples, the product was filtered and characterized by viscosity at 25 ° C., hydroxyl number and appearance (turbid or non-turbid). Lactic acid neutralized samples were not filtered prior to characterization.

  As can be better understood with reference to Table IV, the short chain polyether polyols (Examples 12-15) made with PEG-300 concentrations within the range required by the present invention can be any polyoxyethylene-containing Compared to those prepared without the use of compounds (Examples C-9, C-10 and C-11), the rate was accelerated. Again, the use of PEG-300 resulted in a sample that was not turbid.

  The above embodiments of the present invention are provided for purposes of illustration and not for the purpose of limiting the invention. It will be apparent to those skilled in the art that the embodiments described herein can be varied or modified in various ways without departing from the spirit and scope of the invention. The scope of the invention should be determined by the appended claims.

Claims (44)

  In the presence of a base catalyst having at least one cation chelated with from about 0.5% to about 20% by weight of a polyoxyethylene-containing compound, the weight percent being based on the weight of the short chain polyether polyol. A short chain polyether polyol having a number average molecular weight of less than about 1,200 g / mole produced by alkoxylation of   The short chain polyether polyol of claim 1, having a number average molecular weight of about 300 g / mole to about 1,000 g / mole.   The short chain polyether polyol of claim 1, having a number average molecular weight of about 500 g / mole to about 900 g / mole. The initiator is C ₁ -C ₃₀ monool, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, neopentyl glycol, 1,3-propanediol, 1,4-butanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 1,6-hexanediol, water, glycerin, trimethylolpropane, trimethylolethane, ethylenediamine, toluenediamine isomer, pentaerythritol, α-methyl glucoside, sorbitol, mannitol, hydroxymethyl glucoside, hydroxypropyl glucoside, sucrose, N, N, N ′, N′-tetrakis [2-hydroxyethyl or 2-hydroxypropyl] ethylenediamine, 1,4-cyclohexanediol, Cyclohex Nji methanol, hydroquinone, is selected from resorcinol and mixtures thereof, short chain polyether polyol of Claim 1.   The short-chain polyether polyol according to claim 1, wherein the base catalyst is selected from potassium hydroxide, sodium hydroxide, barium hydroxide and cesium hydroxide.   The short-chain polyether polyol according to claim 1, wherein the base catalyst is potassium hydroxide. Alkylene oxide is ethylene oxide, propylene oxide, oxetane, 1,2- and 2,3-butylene oxide, isobutylene oxide, epichlorohydrin, cyclohexene oxide, styrene oxide, C ₅ -C ₃₀ α-alkylene oxide and mixtures thereof The short-chain polyether polyol according to claim 1, selected from:   The short-chain polyether polyol according to claim 1, wherein the alkylene oxide is propylene oxide.   The short chain polyether polyol of claim 1, wherein at least one cation of the base catalyst is chelated with from about 1% to about 10% by weight of a polyoxyethylene-containing compound.   The short chain polyether polyol of claim 1, wherein at least one cation of the base catalyst is chelated with from about 2% to about 7% by weight of a polyoxyethylene-containing compound.   A method for producing a short chain polyether polyol having a number average molecular weight of less than about 1,200 g / mole, comprising about 0.5 wt% to about 20 wt% (where wt% is based on the weight of the short chain polyether polyol). A method comprising alkoxylating an initiator in the presence of a base catalyst having at least one cation chelated with a polyoxyethylene-containing compound.   12. The method of claim 11, wherein the short chain polyether polyol has a number average molecular weight of about 300 g / mole to about 1,000 g / mole.   12. The method of claim 11, wherein the short chain polyether polyol has a number average molecular weight of about 500 g / mol to about 900 g / mol. Initiator, C ₁ -C ₃₀ monols, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, neopentyl glycol, 1,3-propanediol, 1,4-butanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 1,6-hexanediol, water, glycerin, trimethylolpropane, trimethylolethane, ethylenediamine, toluenediamine isomer, pentaerythritol, α-methyl glucoside, sorbitol, mannitol, hydroxymethyl glucoside, hydroxypropyl glucoside, sucrose, N, N, N ′, N′-tetrakis [2-hydroxyethyl or 2-hydroxypropyl] ethylenediamine, 1,4-cyclohexanediol, Cyclohex Nji methanol, hydroquinone, is selected from resorcinol, and mixtures thereof The method of claim 11.   12. A process according to claim 11, wherein the base catalyst is selected from potassium hydroxide, sodium hydroxide, barium hydroxide and cesium hydroxide.   12. A process according to claim 11 wherein the base catalyst is potassium hydroxide. Alkylene oxide is ethylene oxide, propylene oxide, oxetane, 1,2- and 2,3-butylene oxide, isobutylene oxide, epichlorohydrin, cyclohexene oxide, styrene oxide, C ₅ -C ₃₀ α-alkylene oxide and mixtures thereof The method of claim 11, selected from:   12. A process according to claim 11 wherein the alkylene oxide is propylene oxide.   12. The method of claim 11, wherein at least one cation of the base catalyst is chelated with from about 1% to about 10% by weight of a polyoxyethylene-containing compound.   12. The method of claim 11, wherein at least one cation of the base catalyst is chelated with about 2% to about 7% by weight of a polyoxyethylene-containing compound. At least one polyisocyanate;
In the presence of a base catalyst having at least one cation chelated with from about 0.5% to about 20% by weight of a polyoxyethylene-containing compound, the weight percent being based on the weight of the short chain polyether polyol. With at least one short-chain polyether polyol having a number average molecular weight of less than about 1,200 g / mol, prepared by alkoxylation of
Optionally in the presence of at least one of blowing agents, surfactants, other cross-linking agents, extenders, pigments, flame retardants, catalysts and fillers,
A rigid polyurethane foam comprising a reaction product.   At least one polyisocyanate is ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,12-dodecane diisocyanate, cyclobutane-1,3-diisocyanate, cyclohexane-1,3- and -1. , 4-diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (isophorone diisocyanate), 2,4- and 2,6-hexahydrotoluene diisocyanate, dicyclohexylmethane-4,4 ' -Diisocyanate (hydrogenated MDI or HMDI), 1,3- and 1,4-phenylene diisocyanate, 2,4- and 2,6-toluene diisocyanate (TDI), diphenylmethane-2,4'- and / or -4, 4'-diisocyanate (MDI), polymer diphenylmethane diisocyanate (PMDI), naphthylene-1,5-diisocyanate, Phenyl-methane-4,4 ', 4' '-triisocyanate, polyphenyl-polymethylene-polyisocyanate (crude MDI), norbornane diisocyanate, m- and p-isocyanatophenylsulfonyl isocyanate, perchlorinated aryl polyisocyanate, carbodiimide The rigid of claim 21, selected from a modified polyisocyanate, a urethane-modified polyisocyanate, an allophanate-modified polyisocyanate, an isocyanurate-modified polyisocyanate, a urea-modified polyisocyanate, a biuret-containing polyisocyanate, an isocyanate-terminated prepolymer, and mixtures thereof. Polyurethane foam.   The rigid polyurethane foam according to claim 21, wherein the at least one polyisocyanate is polymeric diphenylmethane diisocyanate (PMDI).   The rigid polyurethane foam of claim 21, wherein the short chain polyether polyol has a number average molecular weight of from about 300 g / mole to about 1,000 g / mole.   The rigid polyurethane foam of claim 21, wherein the short chain polyether polyol has a number average molecular weight of from about 500 g / mole to about 900 g / mole. The initiator is C ₁ -C ₃₀ monool, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, neopentyl glycol, 1,3-propanediol, 1,4-butanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 1,6-hexanediol, water, glycerin, trimethylolpropane, trimethylolethane, ethylenediamine, toluenediamine isomer, pentaerythritol, α-methyl glucoside, sorbitol, mannitol, hydroxymethyl glucoside, hydroxypropyl glucoside, sucrose, N, N, N ′, N′-tetrakis [2-hydroxyethyl or 2-hydroxypropyl] ethylenediamine, 1,4-cyclohexanediol, Cyclohex Nji methanol, hydroquinone, is selected from resorcinol and mixtures thereof, the rigid polyurethane foam according to claim 21.   The rigid polyurethane foam according to claim 21, wherein the base catalyst is selected from potassium hydroxide, sodium hydroxide, barium hydroxide and cesium hydroxide.   The rigid polyurethane foam according to claim 21, wherein the base catalyst is potassium hydroxide. Alkylene oxide is ethylene oxide, propylene oxide, oxetane, 1,2- and 2,3-butylene oxide, isobutylene oxide, epichlorohydrin, cyclohexene oxide, styrene oxide, C ₅ -C ₃₀ α-alkylene oxide and mixtures thereof The rigid polyurethane foam according to claim 21, which is selected from:   The rigid polyurethane foam according to claim 21, wherein the alkylene oxide is propylene oxide.   The rigid polyurethane foam according to claim 21, wherein at least one cation of the base catalyst is chelated with from about 1% to about 10% by weight of a polyoxyethylene-containing compound.   The rigid polyurethane foam according to claim 21, wherein at least one cation of the base catalyst is chelated with from about 2% to about 7% by weight of a polyoxyethylene-containing compound. At least one polyisocyanate;
In the presence of a base catalyst having at least one cation chelated with from about 0.5% to about 20% by weight of a polyoxyethylene-containing compound, the weight percent being based on the weight of the short chain polyether polyol. At least one short-chain polyether polyol having a number average molecular weight of less than about 1,200 g / mole produced by alkoxylation of
Optionally in the presence of at least one of blowing agents, surfactants, other cross-linking agents, extenders, pigments, flame retardants, catalysts and fillers,
A method for producing a rigid polyurethane foam, comprising reacting.   At least one polyisocyanate is ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,12-dodecane diisocyanate, cyclobutane-1,3-diisocyanate, cyclohexane-1,3- and -1. , 4-diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (isophorone diisocyanate), 2,4- and 2,6-hexahydrotoluene diisocyanate, dicyclohexylmethane-4,4 ' -Diisocyanate (hydrogenated MDI or HMDI), 1,3- and 1,4-phenylene diisocyanate, 2,4- and 2,6-toluene diisocyanate (TDI), diphenylmethane-2,4'- and / or -4, 4'-diisocyanate (MDI), polymer diphenylmethane diisocyanate (PMDI), naphthylene-1,5-diisocyanate, Phenyl-methane-4,4 ', 4' '-triisocyanate, polyphenyl-polymethylene-polyisocyanate (crude MDI), norbornane diisocyanate, m- and p-isocyanatophenylsulfonyl isocyanate, perchlorinated aryl polyisocyanate, carbodiimide 34. The method of claim 33, selected from modified polyisocyanates, urethane-modified polyisocyanates, allophanate-modified polyisocyanates, isocyanurate-modified polyisocyanates, urea-modified polyisocyanates, biuret-containing polyisocyanates, isocyanate-terminated prepolymers and mixtures thereof. .   34. The method of claim 33, wherein the at least one polyisocyanate is polymeric diphenylmethane diisocyanate (PMDI).   34. The method of claim 33, wherein the short chain polyether polyol has a number average molecular weight of from about 300 g / mole to about 1,000 g / mole.   34. The method of claim 33, wherein the short chain polyether polyol has a number average molecular weight of about 500 g / mole to about 900 g / mole. The initiator is C ₁ -C ₃₀ monool, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, neopentyl glycol, 1,3-propanediol, 1,4-butanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 1,6-hexanediol, water, glycerin, trimethylolpropane, trimethylolethane, ethylenediamine, toluenediamine isomer, pentaerythritol, α-methyl glucoside, sorbitol, mannitol, hydroxymethyl glucoside, hydroxypropyl glucoside, sucrose, N, N, N ′, N′-tetrakis [2-hydroxyethyl or 2-hydroxypropyl] ethylenediamine, 1,4-cyclohexanediol, Cyclohex Nji methanol, hydroquinone, is selected from resorcinol, and mixtures thereof The method of claim 33.   34. A process according to claim 33, wherein the base catalyst is selected from potassium hydroxide, sodium hydroxide, barium hydroxide and cesium hydroxide.   34. The method of claim 33, wherein the base catalyst is potassium hydroxide. Alkylene oxide is ethylene oxide, propylene oxide, oxetane, 1,2- and 2,3-butylene oxide, isobutylene oxide, epichlorohydrin, cyclohexene oxide, styrene oxide, C ₅ -C ₃₀ α-alkylene oxide and mixtures thereof 34. The method of claim 33, selected from:   34. The method of claim 33, wherein the alkylene oxide is propylene oxide.   34. The method of claim 33, wherein at least one cation of the base catalyst is chelated with from about 1% to about 10% by weight of a polyoxyethylene-containing compound.   34. The method of claim 33, wherein at least one cation of the base catalyst is chelated with from about 2% to about 7% by weight of a polyoxyethylene-containing compound.